DE3787336T2 - Verfahren zur Herstellung von Copolyesters, die Anisotropie in geschmolzenem Zustand zeigen. - Google Patents
Verfahren zur Herstellung von Copolyesters, die Anisotropie in geschmolzenem Zustand zeigen.Info
- Publication number
- DE3787336T2 DE3787336T2 DE87308478T DE3787336T DE3787336T2 DE 3787336 T2 DE3787336 T2 DE 3787336T2 DE 87308478 T DE87308478 T DE 87308478T DE 3787336 T DE3787336 T DE 3787336T DE 3787336 T2 DE3787336 T2 DE 3787336T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- carbon atoms
- radical
- process according
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 22
- 229920001634 Copolyester Polymers 0.000 title claims description 12
- -1 hydroxycarboxylic acid ester Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 20
- 229920000728 polyester Polymers 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 230000005587 bubbling Effects 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 229920000106 Liquid crystal polymer Polymers 0.000 description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- GJLNWLVPAHNBQN-UHFFFAOYSA-N phenyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC=C1 GJLNWLVPAHNBQN-UHFFFAOYSA-N 0.000 description 3
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical class C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ZCGDGMQYRJIQSU-UHFFFAOYSA-N phenyl 6-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC(O)=CC=C2C=C1C(=O)OC1=CC=CC=C1 ZCGDGMQYRJIQSU-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GFHGEIJFEHZKHZ-UHFFFAOYSA-N 2-hydroxyethyl 4-hydroxybenzoate Chemical compound OCCOC(=O)C1=CC=C(O)C=C1 GFHGEIJFEHZKHZ-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61227631A JPH0749472B2 (ja) | 1986-09-26 | 1986-09-26 | コポリエステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3787336D1 DE3787336D1 (de) | 1993-10-14 |
DE3787336T2 true DE3787336T2 (de) | 1994-01-05 |
Family
ID=16863933
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE87308478T Expired - Fee Related DE3787336T2 (de) | 1986-09-26 | 1987-09-25 | Verfahren zur Herstellung von Copolyesters, die Anisotropie in geschmolzenem Zustand zeigen. |
Country Status (5)
Country | Link |
---|---|
US (1) | US4767830A (ko) |
EP (1) | EP0261976B1 (ko) |
JP (1) | JPH0749472B2 (ko) |
KR (1) | KR940010342B1 (ko) |
DE (1) | DE3787336T2 (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5171765A (en) * | 1987-03-27 | 1992-12-15 | North Dakota State University | Water dispersible polymers for coatings based on polymers containing mesogenic groups |
US5218045A (en) * | 1987-03-27 | 1993-06-08 | North Dakota State University | Coating binders comprising liquid crystalline enhanced polymers |
US5244699A (en) * | 1987-03-27 | 1993-09-14 | North Dakota State University | Polymeric vehicle for coatings |
DE3719577A1 (de) * | 1987-06-12 | 1988-12-29 | Bayer Ag | Substituierte aromatische polyester |
US5466744A (en) * | 1990-11-05 | 1995-11-14 | General Electric Company | Polymerization of macrocyclic poly(alkylene dicarboxylate) oligomers |
AU665346B2 (en) * | 1991-03-20 | 1996-01-04 | North Dakota State University | Compounds with liquid crystalline properties and coating binders based thereon |
CA2491910A1 (en) * | 2002-07-12 | 2004-01-22 | E.I. Du Pont De Nemours And Company | Liquid crystalline polymers, processes for their manufacture, and articles thereof |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3288755A (en) * | 1964-02-19 | 1966-11-29 | Inventa Ag | Process for the manufacture of copolyetheresters |
US3778410A (en) * | 1972-09-28 | 1973-12-11 | Eastman Kodak Co | Process for preparing a final copolyester by reacting a starting polyester with an acyloxy aromatic carboxylic acid |
US3975487A (en) * | 1973-08-20 | 1976-08-17 | The Carborundum Company | Process for spinning high modulus oxybenzoyl copolyester fibers |
US4184996A (en) * | 1977-09-12 | 1980-01-22 | Celanese Corporation | Melt processable thermotropic wholly aromatic polyester |
JPS5734123A (en) * | 1980-08-07 | 1982-02-24 | Teijin Ltd | Production of polyester |
JPS60219224A (ja) * | 1984-04-16 | 1985-11-01 | Teijin Ltd | ポリエステルの製造方法 |
US4621126A (en) * | 1984-06-08 | 1986-11-04 | E. I. Du Pont De Nemours And Company | Group transfer polymerization employing tris(disubstituted amino)sulfonium perfluorocarbanion salts as catalysts |
-
1986
- 1986-09-26 JP JP61227631A patent/JPH0749472B2/ja not_active Expired - Lifetime
-
1987
- 1987-09-22 KR KR1019870010483A patent/KR940010342B1/ko active IP Right Grant
- 1987-09-22 US US07/099,891 patent/US4767830A/en not_active Expired - Lifetime
- 1987-09-25 EP EP87308478A patent/EP0261976B1/en not_active Expired - Lifetime
- 1987-09-25 DE DE87308478T patent/DE3787336T2/de not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0261976A3 (en) | 1989-03-08 |
DE3787336D1 (de) | 1993-10-14 |
EP0261976B1 (en) | 1993-09-08 |
US4767830A (en) | 1988-08-30 |
KR880003995A (ko) | 1988-06-01 |
JPH0749472B2 (ja) | 1995-05-31 |
EP0261976A2 (en) | 1988-03-30 |
JPS6383127A (ja) | 1988-04-13 |
KR940010342B1 (ko) | 1994-10-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |